JPS5934704B2 - ３・７ジメチル−３−ヒドロキシ−６−オクテンニトリルノセイホウ - Google Patents
３・７ジメチル−３−ヒドロキシ−６−オクテンニトリルノセイホウInfo
- Publication number
- JPS5934704B2 JPS5934704B2 JP50128986A JP12898675A JPS5934704B2 JP S5934704 B2 JPS5934704 B2 JP S5934704B2 JP 50128986 A JP50128986 A JP 50128986A JP 12898675 A JP12898675 A JP 12898675A JP S5934704 B2 JPS5934704 B2 JP S5934704B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- dimethyl
- minutes
- sodium
- octenitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 dimethyl-3-hydroxy-6-octenenitrile Chemical compound 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LKZJNXXGMPYNJN-UHFFFAOYSA-N 3-hydroxy-3,7-dimethyloct-6-enenitrile Chemical compound CC(C)=CCCC(C)(O)CC#N LKZJNXXGMPYNJN-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT28955/74A IT1025318B (it) | 1974-10-30 | 1974-10-30 | 3.7 dimetil 3 idrossi 6 octenenitri le e procedimento per la sua preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5168524A JPS5168524A (en) | 1976-06-14 |
| JPS5934704B2 true JPS5934704B2 (ja) | 1984-08-24 |
Family
ID=11225032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50128986A Expired JPS5934704B2 (ja) | 1974-10-30 | 1975-10-28 | ３・７ジメチル−３−ヒドロキシ−６−オクテンニトリルノセイホウ |
Country Status (28)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2938689A1 (de) * | 1979-09-25 | 1981-04-09 | Basf Ag, 6700 Ludwigshafen | Aliphatische methoxy- und hydroxynitrile, deren herstellung und deren verwendung als riechstoff |
| US4489009A (en) * | 1982-03-11 | 1984-12-18 | International Flavors & Fragrances Inc. | Process for producing solanone, norsolanadione and intermediates therefor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1356949A (fr) * | 1962-12-13 | 1964-04-03 | Rhone Poulenc Sa | Procédé de préparation de dérivés de l'acide cyclopropanecarboxylique |
| US3755411A (en) * | 1971-02-01 | 1973-08-28 | Zoecon Corp | Halo or oxy substituted aliphatic di olefinic nitriles |
| US3932483A (en) * | 1971-06-02 | 1976-01-13 | Sandoz Ltd., (Sandoz Ag) | W-Aliphatic and cycloaliphatic-hydrocarbonoxy-2,6-alkadiene and 2-alkene-1-nitriles |
-
1974
- 1974-10-30 IT IT28955/74A patent/IT1025318B/it active
-
1975
- 1975-10-07 ZA ZA00756355A patent/ZA756355B/xx unknown
- 1975-10-08 CA CA237,580A patent/CA1047535A/en not_active Expired
- 1975-10-09 IN IN1959/CAL/75A patent/IN146080B/en unknown
- 1975-10-13 GB GB41876/75A patent/GB1494939A/en not_active Expired
- 1975-10-14 TR TR18609A patent/TR18609A/xx unknown
- 1975-10-21 SU SU752182002A patent/SU644379A3/ru active
- 1975-10-21 YU YU2661/75A patent/YU36693B/xx unknown
- 1975-10-22 IE IE2307/75A patent/IE41921B1/en unknown
- 1975-10-23 FR FR7532402A patent/FR2289494A1/fr active Granted
- 1975-10-25 EG EG75633A patent/EG12396A/xx active
- 1975-10-27 BE BE161274A patent/BE834897A/xx not_active IP Right Cessation
- 1975-10-28 JP JP50128986A patent/JPS5934704B2/ja not_active Expired
- 1975-10-28 LU LU73668A patent/LU73668A1/xx unknown
- 1975-10-28 DK DK484375A patent/DK484375A/da not_active Application Discontinuation
- 1975-10-28 DD DD189090A patent/DD123740A5/xx unknown
- 1975-10-28 NL NL7512622.A patent/NL162064C/xx not_active IP Right Cessation
- 1975-10-29 AT AT823075A patent/AT341492B/de not_active IP Right Cessation
- 1975-10-29 PL PL1975184336A patent/PL102201B1/pl unknown
- 1975-10-29 NO NO753642A patent/NO140855C/no unknown
- 1975-10-29 HU HU75SA00002850A patent/HU171174B/hu unknown
- 1975-10-29 SE SE7512122A patent/SE427180B/xx unknown
- 1975-10-29 CS CS757301A patent/CS191953B2/cs unknown
- 1975-10-29 DE DE19752548420 patent/DE2548420A1/de not_active Ceased
- 1975-10-30 BG BG031366A patent/BG25073A3/xx unknown
- 1975-10-30 BR BR7507201*A patent/BR7507201A/pt unknown
- 1975-10-30 ES ES442473A patent/ES442473A1/es not_active Expired
-
1978
- 1978-03-21 US US05/888,533 patent/US4331568A/en not_active Expired - Lifetime
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